Couple of thoughts, the Alaskans were/are very formidable cruising yachts, and from what you've said, this one is in great condition.
C'mon, man- Wood is always better than fiberglass!
Seriously, you have a nice one now, and the older ones ride even BETTER and handle better; BUT, and there's always a but, they are wood. Thus, they come with the inherent differences in maintenance schedules, etc.
Will she be in fresh water? I believe you mentioned covered. AWESOME. I would not keep my wooden boat if it wasn't under cover.
$349,000 for that boat is PREMIUM price, and I doubt, without being for sale for a long time, if you ever would get it back out. ... and that doesn't include the maintenance on top of the price.
You've got to look at what the market will bear- most Alaskans are going for $200,000 range or less. I know, I know, they are not in as nice of shape, but perception is reality.
She'll outlast your fiberglass GB if you keep a decent annual maintenance schedule.
You either love wood, or you don't ... emotion and wood go together, we are a dieing breed, no?
A 1974 boat has typically bottomed-out with regard to depreciation, as long as you pay a reasonable price, and, if anything, it will only go up as it gets older.
VERY IMPORTANT- forget what they tell you about "no expense spared" "finest of everything" la-la-la-la.
Get a very thorough survey, in and OUT of the water with that kind of investment.
If everything checks out as they say, offer them $275,000! They will probably take it, as it's been for sale for a while (probably) and there are not a whole lot of buyers for a 53' Alaskan.
Even if you paid full price, and spared no expense on maintenance, it would be a long time before you'd reach the $700,000 plateau.
Is she checks out, go for it.
Brad
Nothing else matters but how I raise my children ... and their opinion of me, as a father.